This is an important point to me. These people were living (by relative standards, absolutely thriving) with very little income, coasting on what a post-war, peak-cheap-oil society could provide. Sure, in their writing they occasionally questioned the status quo. But reading it in retrospect just highlights how materially lucky they were to have those crazy experiences. Road tripping across the US in search of something greater is a privledge; if I met Dean Moriarty and Jack Kerouac today, I'd probably give them an "OK Boomer" eye roll.
You’re right, but if you study history, you’ll discover that every generation has their own take on this phenomenon.
#vanLife is just the latest version of it. Remember, Dean (Neil) transcended the Beats, became a member of the Merry Pranksters, and drove the bus for Kesey’s hippies who lived in it. It’s all connected.